DM1-SMCC
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    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 407202

CAS#: 1228105-51-8

Description: DM1-SMCC is DM1 with a reactive linker SMCC, which can react with antibody to make antibody drug conjugate. DM1 is an antibody-conjugatable maytansinoid that was developed to overcome systemic toxicity associated with maytansine and to enhance tumor-specific delivery. DM1 binds at the tips of microtubules and suppresses the dynamicity of microtubules.


Chemical Structure

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DM1-SMCC
CAS# 1228105-51-8

Theoretical Analysis

MedKoo Cat#: 407202
Name: DM1-SMCC
CAS#: 1228105-51-8
Chemical Formula: C51H66ClN5O16S
Exact Mass: 1071.39138
Molecular Weight: 1072.618
Elemental Analysis: C, 57.11; H, 6.20; Cl, 3.30; N, 6.53; O, 23.87; S, 2.99

Size Price Shipping out time Quantity
5mg USD 250 Same day
10mg USD 450 Same day
50mg USD 1650 Same day
100mg USD 2650 Same day
200mg USD 3650 Same day
1g USD 5250 2 weeks
2g USD 9850 2 weeks
5g USD 19850 2 weeks
Inquire bulk and customized quantity

Pricing updated 2021-03-02. Prices are subject to change without notice.

DM1-SMCC, purity > 98%, is in stock. The same day shipping out after order is received.

Synonym: DM1-SMCC; DM1 SMCC; DM1SMCC. SMCC-DM1.

IUPAC/Chemical Name: 2,5-dioxopyrrolidin-1-yl 4-((3-((3-(((2S)-1-(((14S,16S,33S,2R,4R,10E,12Z,14R)-86-chloro-14-hydroxy-85,14-dimethoxy-33,2,7,10-tetramethyl-12,6-dioxo-7-aza-1(6,4)-oxazinana-3(2,3)-oxirana-8(1,3)-benzenacyclotetradecaphane-10,12-dien-4-yl)oxy)-1-oxopropan-2-yl)(methyl)amino)-3-oxopropyl)thio)-2,5-dioxopyrrolidin-1-yl)methyl)cyclohexane-1-carboxylate

InChi Key: IADUWZMNTKHTIN-IOBAKXROSA-N

InChi Code: InChI=1S/C51H66ClN5O16S/c1-27-10-9-11-37(69-8)51(67)25-35(70-49(66)53-51)28(2)45-50(4,72-45)38(24-42(61)55(6)33-21-31(20-27)22-34(68-7)44(33)52)71-47(64)29(3)54(5)39(58)18-19-74-36-23-43(62)56(46(36)63)26-30-12-14-32(15-13-30)48(65)73-57-40(59)16-17-41(57)60/h9-11,21-22,28-30,32,35-38,45,67H,12-20,23-26H2,1-8H3,(H,53,66)/b11-9-,27-10+/t28-,29+,30?,32?,35+,36?,37-,38-,45?,50+,51+/m1/s1

SMILES Code: C[C@@H]1[C@@H]2C[C@](NC(O2)=O)(O)[C@H](OC)/C=C\C=C(C)\CC3=CC(N(C)C(C[C@@H](OC([C@@H](N(C(CCSC(C(N4CC5CCC(C(ON6C(CCC6=O)=O)=O)CC5)=O)CC4=O)=O)C)C)=O)[C@@]7(C)C1O7)=O)=C(Cl)C(OC)=C3

Appearance:
White to off-white solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:
Soluble in DMSO, not in water

Shelf Life:
>2 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code:
2934.99.9001

Preparing Stock Solutions

The following data is based on the product molecular weight 1072.618 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Select a batch to recalculate based on the batch molecular weight:
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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1: Sun Y, Liang Y, Dai W, He B, Zhang H, Wang X, Wang J, Huang S, Zhang Q. Peptide-Drug Conjugate-Based Nanocombination Actualizes Breast Cancer Treatment by Maytansinoid and Photothermia with the Assistance of Fluorescent and Photoacoustic Images. Nano Lett. 2019 May 8;19(5):3229-3237. doi: 10.1021/acs.nanolett.9b00770. Epub 2019 Apr 11. PubMed PMID: 30957499.

2: Shao S, Tsai MH, Lu J, Yu T, Jin J, Xiao D, Jiang H, Han M, Wang M, Wang J. Site-specific and hydrophilic ADCs through disulfide-bridged linker and branched PEG. Bioorg Med Chem Lett. 2018 May 1;28(8):1363-1370. doi: 10.1016/j.bmcl.2018.03.005. Epub 2018 Mar 3. PubMed PMID: 29559276.

3: Sun X, Ponte JF, Yoder NC, Laleau R, Coccia J, Lanieri L, Qiu Q, Wu R, Hong E, Bogalhas M, Wang L, Dong L, Setiady Y, Maloney EK, Ab O, Zhang X, Pinkas J, Keating TA, Chari R, Erickson HK, Lambert JM. Effects of Drug-Antibody Ratio on Pharmacokinetics, Biodistribution, Efficacy, and Tolerability of Antibody-Maytansinoid Conjugates. Bioconjug Chem. 2017 May 17;28(5):1371-1381. doi: 10.1021/acs.bioconjchem.7b00062. Epub 2017 Apr 13. PubMed PMID: 28388844.

4: Ponte JF, Sun X, Yoder NC, Fishkin N, Laleau R, Coccia J, Lanieri L, Bogalhas M, Wang L, Wilhelm S, Widdison W, Pinkas J, Keating TA, Chari R, Erickson HK, Lambert JM. Understanding How the Stability of the Thiol-Maleimide Linkage Impacts the Pharmacokinetics of Lysine-Linked Antibody-Maytansinoid Conjugates. Bioconjug Chem. 2016 Jul 20;27(7):1588-98. doi: 10.1021/acs.bioconjchem.6b00117. Epub 2016 Jun 20. PubMed PMID: 27174129.

5: Ogitani Y, Hagihara K, Oitate M, Naito H, Agatsuma T. Bystander killing effect of DS-8201a, a novel anti-human epidermal growth factor receptor 2 antibody-drug conjugate, in tumors with human epidermal growth factor receptor 2 heterogeneity. Cancer Sci. 2016 Jul;107(7):1039-46. doi: 10.1111/cas.12966. Epub 2016 Jun 22. PubMed PMID: 27166974; PubMed Central PMCID: PMC4946713.

6: Salomon PL, Singh R. Sensitive ELISA Method for the Measurement of Catabolites of Antibody-Drug Conjugates (ADCs) in Target Cancer Cells. Mol Pharm. 2015 Jun 1;12(6):1752-61. doi: 10.1021/acs.molpharmaceut.5b00028. Epub 2015 Mar 17. PubMed PMID: 25738394.

7: Goldmacher VS, Amphlett G, Wang L, Lazar AC. Statistics of the distribution of the abundance of molecules with various drug loads in maytansinoid antibody-drug conjugates. Mol Pharm. 2015 Jun 1;12(6):1738-44. doi: 10.1021/mp5007536. Epub 2015 Feb 17. PubMed PMID: 25635630.

8: Deckert J, Park PU, Chicklas S, Yi Y, Li M, Lai KC, Mayo MF, Carrigan CN, Erickson HK, Pinkas J, Lutz RJ, Chittenden T, Lambert JM. A novel anti-CD37 antibody-drug conjugate with multiple anti-tumor mechanisms for the treatment of B-cell malignancies. Blood. 2013 Nov 14;122(20):3500-10. doi: 10.1182/blood-2013-05-505685. Epub 2013 Sep 3. PubMed PMID: 24002446.

9: Kellogg BA, Garrett L, Kovtun Y, Lai KC, Leece B, Miller M, Payne G, Steeves R, Whiteman KR, Widdison W, Xie H, Singh R, Chari RV, Lambert JM, Lutz RJ. Disulfide-linked antibody-maytansinoid conjugates: optimization of in vivo activity by varying the steric hindrance at carbon atoms adjacent to the disulfide linkage. Bioconjug Chem. 2011 Apr 20;22(4):717-27. doi: 10.1021/bc100480a. Epub 2011 Mar 22. PubMed PMID: 21425776.

10: Oroudjev E, Lopus M, Wilson L, Audette C, Provenzano C, Erickson H, Kovtun Y, Chari R, Jordan MA. Maytansinoid-antibody conjugates induce mitotic arrest by suppressing microtubule dynamic instability. Mol Cancer Ther. 2010 Oct;9(10):2700-13. doi: 10.1158/1535-7163.MCT-10-0645. PubMed PMID: 20937595; PubMed Central PMCID: PMC2976674.

11: Erickson HK, Widdison WC, Mayo MF, Whiteman K, Audette C, Wilhelm SD, Singh R. Tumor delivery and in vivo processing of disulfide-linked and thioether-linked antibody-maytansinoid conjugates. Bioconjug Chem. 2010 Jan;21(1):84-92. doi: 10.1021/bc900315y. PubMed PMID: 19891424.

12: Ikeda H, Hideshima T, Fulciniti M, Lutz RJ, Yasui H, Okawa Y, Kiziltepe T, Vallet S, Pozzi S, Santo L, Perrone G, Tai YT, Cirstea D, Raje NS, Uherek C, Dälken B, Aigner S, Osterroth F, Munshi N, Richardson P, Anderson KC. The monoclonal antibody nBT062 conjugated to cytotoxic Maytansinoids has selective cytotoxicity against CD138-positive multiple myeloma cells in vitro and in vivo. Clin Cancer Res. 2009 Jun 15;15(12):4028-37. doi: 10.1158/1078-0432.CCR-08-2867. Epub 2009 Jun 9. PubMed PMID: 19509164.

13: Erickson HK, Park PU, Widdison WC, Kovtun YV, Garrett LM, Hoffman K, Lutz RJ, Goldmacher VS, Blättler WA. Antibody-maytansinoid conjugates are activated in targeted cancer cells by lysosomal degradation and linker-dependent intracellular processing. Cancer Res. 2006 Apr 15;66(8):4426-33. PubMed PMID: 16618769.